JP2008074723A - Method for producing solubilized nobiletin composition - Google Patents
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本発明は、可溶化ノビレチン組成物の製造方法に関し、より詳しくは、有機溶媒を含まないため安全性が高く、また水への溶解性に優れるとともに、ノビレチンの苦味も低減された可溶化ノビレチン組成物の製造方法に関する。 The present invention relates to a method for producing a solubilized nobiletin composition, and more specifically, a solubilized nobiletin composition having high safety because it does not contain an organic solvent, excellent solubility in water, and reduced bitterness of nobiletin. The present invention relates to a method for manufacturing a product.
沖縄県に多産する柑橘類であるシークワーサーやタンカンには、ポリアルコキシフラボノイドであるノビレチンやタンゲレチンが多く含まれる。ノビレチンには抗がん効果があることが知られており、また血糖値低下作用および血圧低下作用を有することも報告されている（特許文献１参照）。 Sikhwasa and Tankan, citrus fruits that are prolific in Okinawa, are rich in polyalkoxyflavonoids, nobiletin and tangeretin. Nobiletin is known to have an anticancer effect, and has been reported to have a blood glucose level lowering action and a blood pressure lowering action (see Patent Document 1).
また、ノビレチンには、リン脂質を分解しアラキドン酸を生成する酵素（細胞質リン脂質分解酵素）を阻害し、さらにノビレチンは、アラキドン酸から生成する回路のキー酵素である誘導性シクロオキシゲナーゼ（ＣＯＸ−２）により紫外線で誘導されるプロスタグランジンＥ２を抑制することから、紫外線照射による障害を予防できることが報告されている（特許文献２参照）。このような機能性を有することから、ノビレチンは近年注目を集めている。 In addition, nobiletin inhibits an enzyme that generates arachidonic acid by decomposing phospholipid (cytoplasmic phospholipidase), and nobiletin is an inducible cyclooxygenase (COX-2) that is a key enzyme in a circuit generated from arachidonic acid. ) Suppresses the prostaglandin E2 induced by ultraviolet rays, and it has been reported that damage caused by ultraviolet irradiation can be prevented (see Patent Document 2). Nobiletin has attracted attention in recent years because of its functionality.
ところで、このノビレチンは難水溶性であるため、その製造は主にシークワーサーやタンカンを有機溶媒で抽出する方法によって行われている。また、シークワーサーに超臨界状態の炭酸ガスを接触させることによりノビレチンを抽出する方法が開発されている。しかしながら、これらの方法によって得られたノビレチンは難水溶性であるため、水溶液としての利用は難しいという問題があった。 By the way, since this nobiletin is sparingly water-soluble, its production is mainly carried out by a method of extracting seeker or tankan with an organic solvent. In addition, a method for extracting nobiletin by contacting a seeker with carbon dioxide in a supercritical state has been developed. However, since nobiletin obtained by these methods is poorly water-soluble, there is a problem that it is difficult to use as an aqueous solution.
一方、ノビレチンなどのフラボン誘導体のシクロデキストリン包接物の製造方法が開示されている（特許文献３参照）。しかしながら、この製造方法では、溶媒としてエタノール水溶液を用いているため、サイクロデキストリンと有機溶媒の包接物が形成され、その後エバポレーターなどにより有機溶媒を完全に除去することは困難であり安全性の面で問題があった。また水溶性のノビレチン包接体がほとんど形成されないため水溶液としての利用が困難であった。 On the other hand, a method for producing a cyclodextrin inclusion product of a flavone derivative such as nobiletin has been disclosed (see Patent Document 3). However, in this production method, since an aqueous ethanol solution is used as a solvent, a clathrate of cyclodextrin and an organic solvent is formed, and thereafter it is difficult to completely remove the organic solvent with an evaporator or the like. There was a problem. Further, since a water-soluble nobiletin inclusion body is hardly formed, it is difficult to use it as an aqueous solution.
したがって、有機溶媒を含有せず、また水への溶解性に優れるノビレチン組成物の提供が求められており、本発明はそのような可溶化ノビレチン組成物の製造方法を提供することをその課題とする。 Accordingly, there is a need to provide a nobiletin composition that does not contain an organic solvent and is excellent in solubility in water, and the present invention aims to provide a method for producing such a solubilized nobiletin composition. To do.
本発明者は、上記課題を解決すべく鋭意研究を行った結果、有機溶媒を含有しない水溶液中において、サイクロデキストリンとノビレチンの包接体を形成させることにより、その包接体が水への溶解性に優れ、ノビレチンに固有の苦味も低減できることを見出し、本発明を完成するに至った。 As a result of diligent research to solve the above problems, the present inventor formed a clathrate of cyclodextrin and nobiletin in an aqueous solution not containing an organic solvent, so that the clathrate was dissolved in water. The present invention was completed by finding that it has excellent properties and can reduce the bitterness inherent to nobiletin.
すなわち本発明は、ノビレチンまたはノビレチン含有物を、水とサイクロデキストリンの存在下で有機溶媒を用いることなく包接化処理することを特徴とする可溶化ノビレチン組成物の製造方法である。 That is, the present invention is a method for producing a solubilized nobiletin composition characterized in that nobiletin or a nobiletin-containing material is subjected to inclusion treatment in the presence of water and cyclodextrin without using an organic solvent.
本発明の製造方法によれば、有機溶媒が残存していないため安全性が高く、さらに水への溶解性に優れ、ノビレチンの苦味も低減された可溶化ノビレチン組成物を得ることができる。 According to the production method of the present invention, it is possible to obtain a solubilized nobiletin composition that has high safety because no organic solvent remains, is excellent in solubility in water, and has reduced bitterness of nobiletin.
本発明の製造方法においては、原料としてノビレチンまたはノビレチン含有物が用いられる。前記ノビレチンは、合成されたものであっても、ノビレチンを含有する植物などから精製されたものであってもよい。 In the production method of the present invention, nobiletin or a nobiletin-containing material is used as a raw material. The nobiletin may be synthesized or may be purified from a plant containing nobiletin.
前記のノビレチン含有物とは、ノビレチンを含有する植物（以下、「ノビレチン含有植物」という）そのものや、これを様々な形態に加工したものが含まれる。このノビレチン含有植物としては、例えば、シークワーサー、タンカンなどが挙げられ、これらの植物の果実部分などをそのまま用いることができるが、さらに常法により乾燥、粉砕して２ないし４ｍｍ程度のチップや粉末状等の形態にしたものを用いることができる。 The above-mentioned nobiletin-containing product includes a plant containing nobiletin (hereinafter referred to as “nobiletin-containing plant”) itself and those obtained by processing the plant into various forms. Examples of this nobiletin-containing plant include seekers, tankans, and the like, and the fruit portions of these plants can be used as they are, but they are further dried and pulverized by conventional methods to obtain chips and powders of about 2 to 4 mm. The thing of the form of etc. can be used.
また、ノビレチン含有植物を適当な抽出方法により抽出したノビレチン抽出液をノビレチン含有物として用いることもできる。より具体的には、例えば、ノビレチン含有植物を、その２重量倍以上の２０〜５０％のエタノール水溶液に浸漬し、２５〜３０℃程度で１２〜２４時間抽出し、次いでエタノールを常法により除去するエタノール抽出法や、例えば、ノビレチン含有植物に対し、通常０．０１〜０．０５重量倍、好ましくは０．０１〜０．０２重量倍の二酸化炭素を用いて、通常１０〜２０ＭＰａ、好ましくは１２〜１５ＭＰａ程度の圧力、通常３０〜４０℃、好ましくは３５〜４０℃の温度で抽出する二酸化炭素超臨界抽出法により得られる抽出液をノビレチン含有物として用いることができる。 Moreover, the nobiletin extract which extracted the nobiletin containing plant by the suitable extraction method can also be used as a nobiletin containing material. More specifically, for example, a nobiletin-containing plant is immersed in a 20 to 50% ethanol aqueous solution of 2 times or more by weight, extracted at about 25 to 30 ° C. for 12 to 24 hours, and then ethanol is removed by a conventional method. Ethanol extraction method or, for example, 0.01 to 0.05 times by weight, preferably 0.01 to 0.02 times by weight of carbon dioxide with respect to nobiletin-containing plants, usually 10 to 20 MPa, preferably An extract obtained by a carbon dioxide supercritical extraction method which is extracted at a pressure of about 12 to 15 MPa, usually 30 to 40 ° C., preferably 35 to 40 ° C. can be used as the nobiletin-containing material.
本発明の製造方法は、上記ノビレチンまたはノビレチン含有物を、水とサイクロデキストリン（以下、「ＣＤ」ということがある）の存在下で有機溶媒を用いることなく包接化処理を行うものである。 In the production method of the present invention, the nobiletin or the nobiletin-containing material is subjected to an inclusion treatment without using an organic solvent in the presence of water and cyclodextrin (hereinafter sometimes referred to as “CD”).
上記水としては、特に限定されるものではなく、蒸留水、精製水等が用いられる。また、ノビレチン含有物が水溶液である場合には、別途水を添加せず、この水溶液に直接サイクロデキストリンを溶解させることもできる。 The water is not particularly limited, and distilled water, purified water and the like are used. When the nobiletin-containing material is an aqueous solution, the cyclodextrin can be directly dissolved in this aqueous solution without adding water separately.
また上記サイクロデキストリンとしては、α、β、γ−サイクロデキストリンのいずれも用いることができるが、このうち、α、γ−サイクロデキストリンを用いると可溶化包接体が多く形成されるため好ましく、γ−サイクロデキストリンが特に好ましい。 As the cyclodextrin, any of α, β, and γ-cyclodextrin can be used. Of these, α, γ-cyclodextrin is preferable because many solubilized clathrate are formed, and γ Cyclodextrin is particularly preferred.
上記ノビレチンまたはノビレチン含有物を前記水とサイクロデキストリンの存在下で包接化処理する方法としては、水とサイクロデキストリンを同時にノビレチンまたはノビレチン含有物に添加する方法、ノビレチンまたはノビレチン含有物の水溶液にサイクロデキストリンを添加する方法、ノビレチンまたはノビレチン含有物にサイクロデキストロン水溶液を添加する方法などが挙げられる。ノビレチンまたはノビレチン含有物に対する水の量は、ノビレチン含有物の形態等によって適宜設定することができるが、通常ノビレチンまたはノビレチン含有物の１〜４重量倍、好ましくは、１〜２重量倍である。また、ノビレチンまたはノビレチン含有物に対するサイクロデキストリンの量も、ノビレチン含有物の形態等によって適宜設定できるが、通常１〜４重量倍、好ましくは、１〜２重量倍である。 The nobiletin or nobiletin-containing product is included in the inclusion of water and cyclodextrin in the presence of water and cyclodextrin simultaneously to the nobiletin or nobiletin-containing product, or a nobiletin or nobiletin-containing product in an aqueous solution. Examples thereof include a method of adding dextrin, a method of adding a cyclodextron aqueous solution to nobiletin or a nobiletin-containing material, and the like. The amount of water relative to nobiletin or a nobiletin-containing material can be appropriately set depending on the form of the nobiletin-containing material, etc., but is usually 1 to 4 times, preferably 1 to 2 times the weight of nobiletin or the nobiletin-containing material. The amount of cyclodextrin with respect to nobiletin or a nobiletin-containing product can also be appropriately set depending on the form of the nobiletin-containing product, etc., but is usually 1 to 4 times by weight, and preferably 1 to 2 times by weight.
具体的には、例えば、ノビレチン含有物としてタンカンチップ（大きさ３ｍｍ、水分６０％）を用いた場合、タンカンチップ１０ｇに対してサイクロデキストリンを１０〜４０ｇ用いることが好ましく、２０〜２５ｇがより好ましい。一方、タンカン抽出物（２０％エタノール抽出法による抽出液）１０ｇに対してサイクロデキストリンを１０〜４０ｇ使用することが好ましく、２５〜３０ｇ使用することがより好ましい。 Specifically, for example, when a tankan chip (size 3 mm, moisture 60%) is used as the nobiletin-containing material, it is preferable to use 10 to 40 g of cyclodextrin with respect to 10 g of the tankan chip, and more preferably 20 to 25 g. . On the other hand, it is preferable to use 10 to 40 g of cyclodextrin, more preferably 25 to 30 g, based on 10 g of the tankan extract (extracted solution by 20% ethanol extraction method).
本発明の製造方法は、上記包接化処理において有機溶媒を用いないものである。すなわち、一般的にノビレチンの抽出においては、ノビレチンが難水溶性であるため、エタノール等の有機溶媒を用いて抽出するが、有機溶媒が存在しているとサイクロデキストリンと包接体を形成してしまって、その後この有機溶媒を除去することが困難となる。本発明では、有機溶媒を用いることなく水とサイクロデキストリンの存在下ノビレチンを包接化処理するため、有機溶媒が残存せず安全性の高いものとすることができ、さらに水への溶解性の高いノビレチン組成物が得られる。 In the production method of the present invention, an organic solvent is not used in the inclusion treatment. That is, in general, in the extraction of nobiletin, since nobiletin is poorly water-soluble, it is extracted using an organic solvent such as ethanol, but if an organic solvent is present, it forms a clathrate with a cyclodextrin. After that, it becomes difficult to remove the organic solvent thereafter. In the present invention, since nobiletin is clathrated in the presence of water and cyclodextrin without using an organic solvent, the organic solvent does not remain and can be made highly safe, and further has solubility in water. A high nobiletin composition is obtained.
上記のようにして得られた可溶化ノビレチン組成物は、そのまま液状物として用いることもできるが、さらに必要に応じて常法により精製してもよく、さらにまた凍結乾燥等の手段により乾燥させた粉末状のものとしてもよい。またノビレチンは特有の苦味を有するものであるが、この可溶化ノビレチン組成物は、苦味が低減されたものである。 The solubilized nobiletin composition obtained as described above can be used as a liquid as it is, but may be further purified by a conventional method if necessary, and further dried by means such as lyophilization. It is good also as a powder form. Nobiletin has a unique bitter taste, but this solubilized nobiletin composition has a reduced bitter taste.
次に製造例等により本発明を更に詳しく説明するが、本発明はこれら製造例等に何ら制約されるものではない。 Next, the present invention will be described in more detail with reference to production examples, but the present invention is not limited to these production examples.
製 造 例 １
α−ＣＤ、β−ＣＤ、γ−ＣＤの、２．５４ｇ、０．３８ｇ、５．１２ｇを水２０ｍＬに溶解した（この量は、２０ｍＬの水に対するそれぞれの飽和溶解量である）。この各ＣＤ水溶液１０ｍＬにノビレチン（和光純薬（株）製）５ｍｇを加え、２５℃において４８時間スターラーで攪拌し混合液を得た。それぞれの混合液５００μＬを取り、フィルターでろ過した。ろ液中に含まれるノビレチン含有量を下記条件によりＨＰＬＣで測定した。結果を表１に示す。なお、ＣＤを溶解させない蒸留水をコントロールとした。
Manufacturing example 1
2.54 g, 0.38 g, and 5.12 g of α-CD, β-CD, and γ-CD were dissolved in 20 mL of water (this amount is the respective saturated dissolution amount in 20 mL of water). To 10 mL of each CD aqueous solution, 5 mg of nobiletin (manufactured by Wako Pure Chemical Industries, Ltd.) was added and stirred with a stirrer at 25 ° C. for 48 hours to obtain a mixed solution. 500 μL of each mixture was taken and filtered through a filter. The content of nobiletin contained in the filtrate was measured by HPLC under the following conditions. The results are shown in Table 1. Distilled water that does not dissolve CD was used as a control.
＜ＨＰＬＣ条件＞
カラム：Ｃｒｅｓｔ Ｐａｋ Ｃ１８Ｓ
移動相：アセトニトリル：水＝４０：６０
カラム温度：４０℃
流速：１．０ｍＬ／ｍｉｎ
<HPLC conditions>
Column: Crest Pak C18S
Mobile phase: acetonitrile: water = 40: 60
Column temperature: 40 ° C
Flow rate: 1.0 mL / min
表１の結果から明らかなように、α、β、γ−ＣＤを添加したものはいずれもコントロールに比べノビレチン含有量が増加した。特にγ−ＣＤを添加した場合は、コントロールの１４.５倍と最もノビレチンの溶解量を増大させることができた。 As is clear from the results in Table 1, the content of nobiletin increased as compared with the control in the case where α, β and γ-CD were added. In particular, when γ-CD was added, the amount of nobiletin dissolved could be increased the most by 14.5 times that of the control.
試 験 例 １
製造例１で得られた各水溶液をノビレチン含有量が０．０７ｍｇ／１０ｍｌになるように希釈しパネラーによって苦味に関し官能評価した。評価は下記の５段階で評価し、それぞれの平均値を求めた。結果を表２に示す。
（評価）
５：強い苦味を感じた
４：苦味を感じた
３：少し苦味を感じた
２：苦味を感じない
１：完全に苦味を感じない
Test example 1
Each aqueous solution obtained in Production Example 1 was diluted so that the nobiletin content was 0.07 mg / 10 ml, and the panel was subjected to sensory evaluation regarding bitterness. Evaluation was performed in the following five stages, and the average value of each was obtained. The results are shown in Table 2.
(Evaluation)
5: I felt a strong bitterness 4: I felt a bitterness 3: I felt a little bitterness 2: I didn't feel a bitterness 1: I didn't feel a bitterness completely
表２から明らかなように、このノビレチン水溶液はノビレチンの苦味を低下させていることがわかった。 As apparent from Table 2, it was found that this nobiletin aqueous solution reduced the bitterness of nobiletin.
本発明の製造方法は、有機溶媒を含まないため安全性が高く、また水への溶解性に優れ、かつノビレチンの苦味も低減された可溶化ノビレチン組成物を得ることができるものである。 The production method of the present invention can provide a solubilized nobiletin composition having high safety because it does not contain an organic solvent, excellent solubility in water, and reduced bitterness of nobiletin.
従って、本発明の製造方法によって得られた可溶化ノビレチン組成物は、飲食品等に好適に利用できるものである。
以 上
Therefore, the solubilized nobiletin composition obtained by the production method of the present invention can be suitably used for food and drink.
more than
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| JP2009067755A (en) * | 2007-09-18 | 2009-04-02 | South Product:Kk | Method for extracting polymetoxyflavonoid |
| JP2010209029A (en) * | 2009-03-12 | 2010-09-24 | Nagase Iyakuhin Kk | Pharmaceutical composition or health food with improved taste |
| JP2012056938A (en) * | 2010-08-11 | 2012-03-22 | Japan Royal Jelly Co Ltd | Method for producing nobiletin, and nobiletin-containing extract |
| WO2012105546A1 (en) | 2011-01-31 | 2012-08-09 | 株式会社シクロケムバイオ | Process for producing aqueous solution containing fat-soluble substance |
| WO2014103410A1 (en) * | 2012-12-26 | 2014-07-03 | 森永乳業株式会社 | Igf-1 production promoter |
| US20150328182A1 (en) * | 2012-12-26 | 2015-11-19 | Morinaga Milk Industry Co., Ltd. | Igf-1 production-promoting agent |
| AU2013367872B2 (en) * | 2012-12-26 | 2016-05-12 | Morinaga Milk Industry Co., Ltd. | Igf-1 production-promoting agent |
| EP2939672A4 (en) * | 2012-12-26 | 2016-08-17 | Morinaga Milk Industry Co Ltd | Igf-1 production promoter |
| JPWO2014103410A1 (en) * | 2012-12-26 | 2017-01-12 | 森永乳業株式会社 | IGF-1 production promoter |
| US9801404B2 (en) | 2012-12-26 | 2017-10-31 | Morinaga Milk Industry Co., Ltd. | IGF-1 production-promoting agent |
| JP2016003223A (en) * | 2014-06-19 | 2016-01-12 | 株式会社ファンケル | Flavonoid-containing powder composition |
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